Key West

The water is the draw here, not the sand. The sea around the island is warm most of the year, about 30°C in late summer and rarely below 22°C in winter, and it is calm because the reef offshore takes the swell. The town's own beaches are small and modest, though. Smathers Beach on the south shore is a long strip of imported sand, Higgs Beach is a local spot by the old pier, and Fort Zachary Taylor has the clearest water but a rocky, coral-rubble shore where water shoes help.

Shallow seagrass flats and seaweed washing in after storms mean the island is better for floating and snorkelling than for long swims or wading out over soft sand. For a classic beach day, Bahia Honda State Park is about an hour's drive up the Overseas Highway. Most visitors spend their water time on boat trips rather than on a towel.

Key West eats from the sea and from Cuba, which is closer than Miami. Pink shrimp, grouper, snapper, stone crab in the cooler months and conch fritters fill the menus, and Key lime pie is a matter of local pride, argued over by the slice. Cuban sandwiches and small, strong café con leche from takeaway windows are the real morning ritual, and chickens wander between outdoor tables.

The best eating tends to be casual: dockside fish shacks around the Historic Seaport and Bahama Village, and a handful of more ambitious dining rooms in Old Town. Duval Street itself is mostly bar food and frozen drinks at resort prices. It is a pleasant town to eat in for a few days, but the range is narrow and there is little depth beyond seafood and island comfort food.

The town itself is the main sight. Old Town is one of the largest districts of historic wooden buildings in the United States: white conch cottages with louvred shutters, Victorian mansions with deep verandas, and cigar-era houses shaded by banyans and poincianas. Walking its side streets is the best way to understand the place.

The set pieces are small but characterful. The Ernest Hemingway Home, with its colony of six-toed cats, the Harry S. Truman Little White House, the lighthouse museum, Audubon House and the shipwreck treasure collections tell the island's story of wreckers, writers and presidents. Fort Zachary Taylor is a Civil War brick fort, and the Southernmost Point buoy draws a queue for photos. Two days covers it comfortably.

Drinking is part of the island's identity. Duval Street is a long run of open-sided bars, rooftop decks and old saloons where you carry a drink from one to the next, and the bars stay open into the small hours. The evening starts at sunset on Mallory Square and moves inland from there, and the crowd mixes cruise passengers, fishermen, bachelor parties and a long-established gay scene at the upper end of Duval.

The tone is loud, loose and boozy rather than stylish, and there are few real clubs. Fantasy Fest in late October and the winter high season are the liveliest times, while late summer is quieter. Anyone looking for cocktail craft or dance music will find the range limited, but as a place to stay out late and in shorts it has a reputation that far exceeds its size.

Key West's outdoors is almost all water. A few kilometres offshore lies the Florida Reef, a coral barrier reef reached by snorkelling and diving boats that leave the harbour daily, with parrotfish, rays and turtles in clear, warm water. Backcountry flats and mangrove islands to the north are good for kayaking, paddleboarding and sight-fishing for tarpon, bonefish and permit, and offshore sport fishing is a long tradition.

The Dry Tortugas National Park, a cluster of remote islands reached by ferry or seaplane, offers some of the clearest water and best birdwatching in the region. On land there is little: the island is flat, the parks are small, and hiking does not really exist. Key deer can be seen on Big Pine Key, about thirty minutes up the highway.

Key West sits at the end of a long road, and there is little to visit as a separate trip. The standout is Fort Jefferson in the Dry Tortugas, a vast unfinished nineteenth-century brick fort on a tiny island, a little over two hours away by ferry and a memorable day out.

Otherwise, the Overseas Highway leads past a string of small island towns. Marathon, about an hour away, and Islamorada, nearer two, have marinas, a turtle hospital and a handful of museums, and the drive across the Seven Mile Bridge is a sight in itself. Miami and the Everglades are more than three hours away, too far for a comfortable day.

Families can have a good time here, but the island is not designed around them. The appeal for children is the water: calm shallows at Fort Zachary Taylor, glass-bottom boat and snorkelling trips to the reef, and the Dry Tortugas ferry. In town there is a small aquarium, a butterfly and nature conservatory, the shipwreck museum and the Hemingway cats, and the trolley tours suit younger children.

The flip side is Duval Street, where the drinking starts early and gets louder after dark, and Fantasy Fest is firmly adult. Old Town's quiet residential streets and bike-friendly scale help, and the heat in summer needs planning.

Within the island, getting around is simple. Old Town is compact and flat, and most sights, bars and the harbour lie within a short walk of Duval Street. Bicycles are the local way to travel, and rental bikes, electric carts and scooters are everywhere. A car is more trouble than help in the centre, where parking is scarce and streets are narrow.

Public transport is thin: a small local bus service and sightseeing trolleys rather than a network you would rely on. Heat and sudden summer downpours make midday walking tiring. Reaching the rest of the Keys means driving the single Overseas Highway or booking a shuttle, and Bahia Honda or Big Pine are hard to reach without wheels.

Shopping is mostly about souvenirs. Duval Street is lined with T-shirt shops, hat stands and Key lime everything, from pies to soap. More interesting are the art galleries in Old Town, which sell tropical painting, prints and local craft, the hand-rolled cigars that recall the island's cigar-making past, and the sponge and shell shops around the harbour.

There are no department stores or fashion streets of note, and resort wear is the closest thing to style. Treat browsing as part of an evening walk rather than a reason to come.

Key West is an expensive place to stay. Land is limited, building is restricted and demand is strong, so rooms, from guesthouses in old conch houses to waterfront resorts, cost far more than in most American cities, and winter and long weekends push them higher still. Eating out and drinking on Duval carry resort prices, and boat trips, diving and the Dry Tortugas ferry add up quickly.

What saves money is the island's scale: you can walk or cycle everywhere, the sunset on Mallory Square is free, and Cuban takeaway windows and fish shacks are fair. Late summer, the hot and stormy season, is the cheapest time to come.

Live music is everywhere but rarely serious. Singer-songwriters, cover bands and island-rock acts play in the open-air bars along Duval Street every night, and the island has long attracted songwriters. Drag cabaret is a long-running local tradition with nightly shows. At sunset, Mallory Square fills with jugglers, tightrope walkers, musicians and trained-cat acts, a performance the whole town turns up for.

The formal scene is small: the Tennessee Williams Theatre and a couple of intimate playhouses stage plays and touring shows, and a symphony orchestra performs in the winter season. There is no opera or major concert hall, and summer programming is thin.

Key West has a reputation for slowing down, and away from Duval Street it earns it. The quiet lanes of Old Town, guesthouses built around small pools and gardens, and the habit of stopping everything for sunset all make for an unhurried stay. Resort hotels have spas, and massage and yoga are easy to find.

There is no bathing tradition, however, no thermal waters or bathhouse culture, and the party side of the island is never far away, particularly at weekends and during festivals. The calmest stays are in the residential streets away from the bars, in the quieter months outside winter.